When it comes to Donald Trump, let’s just say libertarians have a complex relationship. In the past, he’s voiced support for legalizing drugs. More recently, he’s expressed an interest in waterboarding and worse. Last month, Trump included in his spate of transition-team meetings John Allison, the former head of the Cato Institute, the marquee libertarian think tank. But he’s also flouting free markets by celebrating his own deal with Carrier to keep 1,000 jobs in the United States. Trump’s pro-Wall Street one minute, and anti-Federal Reserve the next. He’s softer on gay marriage than on abortion. And while he’s got longtime libertarian visionary Peter Thiel in his corner, he’s also got customary press freedom in his crosshairs. Will a Trump presidency tip into authoritarianism, or will it forge some strange but half-recognizable consensus around social liberalism and economic growth?

Libertarians — and not just libertarians — are asking themselves. And though it’s harder than many would hope to settle on some answers, it’s clear what kinds of opportunities Trump could take advantage of or reject. And given the huge questions Obama has left behind about how to restore America’s footing in our technological age, it’s equally clear that political freedom as we have known it could hang in the balance.

Consider the military. Trump’s choice for secretary of Defense is Marine Gen. James “Mad Dog” Mattis, known for his colorful and no-nonsense approach to, well, everything. For libertarians concerned that Trump could fill his Cabinet with people who care a lot more about the war on terror than on civil liberties (ahem, Rudy Giuliani), the move instantly raised some eyebrows. On the other hand, the main thing we know about the influence of Mattis on Trump is that the gruff warrior talked him out of waterboarding in about five minutes.

Trump told the New York Times Mattis said he “never found it to be useful,” claming he could “do better” with “a pack of cigarettes and a couple of beers” than with torture. In typical style, Trump didn’t say he’d changed his feelings about waterboarding, but allowed that he was impressed. Libertarians on edge should probably take solace in the fact that the authority of career professionals like Mattis will likely matter a lot more than Trump’s opinions over the haul of defense policymaking. But how much a fight Trump might put up if he’s annoyed by that fact is up to Trump himself — and, perhaps, his inner circle.

Even inside Trump Tower, however, a certain ambiguity about the upshot of political freedom haunts the proceedings. To manage the transition between Obama and Trump at the Defense Department, Trump has tapped Trae Stephens, an alum of Thiel’s defense-heavy data crunching company Palantir. Thiel’s Silicon Valley relationships also extend past the Pentagon, in the direction of the U.S. intelligence community. Beyond related work at Palantir, his Founders Fund helped supply investment capital to Elon Musk’s SpaceX — which not long ago took the lead in launching orbital satellites away from the Russians. The issue of cybersecurity, one of the Obama administration’s weakest areas, has complicated what was once a very direct libertarian story about privacy and secrecy. (Dramatizing today’s messy new reality, the rogue Anonymous hacking organization has come out in favor of libertarian presidential hopeful John McAfee for Trump security adviser.) If the big tech companies’ complicity in wide-net surveillance was one of the rudest awakenings for libertarians of the past several years, the next few could prove decisive in determining how the balance between protective measures and more oppressive ones is struck, even with a critical mass of libertarians and sympathizers “in the room” with Trump.

The same goes for the coming reckoning over finance, which has been as scrambled and troubled by revolutionary technological advances as security. At a moment when libertarians could split on issues ranging from the phaseout of paper currency to the breakup of the big banks, Trump will be coming into office with a possibly unique and unprecedented opportunity to pick winners and losers in the broad conflict between the country’s established financiers and its virtuoso outsiders. (Thiel’s original goal with PayPal, recall, was to create a method of payment that would replace government currency.) It’s true that Allison, the Ayn Rand fan who suggested to Trump that he scrap Dodd-Frank on grounds of ineffectiveness, lost out in the Treasury Secretary race to Steve Mnuchin, a Goldman Sachs alum seen as a champion of the East Coast power elite. Then again, who better than the likes of Mnuchin to guide Trump away from a destructive approach to the country’s well-established free trade agreements libertarians love? Much as with security, on finance, while presidential authoritarianism might hold out the promise of convenience to Trump, who probably has little patience for parsing the nettlesome challenges posed to policymaking by the tech revolution, a more sophisticated approach to breaking with Obama’s legacy would bear more fruit.

That’s why it’s even worth thinking so hard about which choices would harrow libertarians and which would hearten them. The fact is that libertarians are at the center of the most significant debates about rebuilding the American institutional order on firmer, more durable, and more broadly empowering ground. That means libertarians are best positioned today for more influence — and more variation and nuance in their specific prescriptions around policy. And that, in turn, means they’re perhaps the most important bellwether today in helping Americans get a feel for whether Trump is headed down a path that will lead to peace and prosperity — or to something else.